Discover Casco Bay In Style

private island tours from portland, maine

Set sail from Portland, Maine, and explore the stunning islands, historic lighthouses, and scenic waters of Casco Bay.

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Explore the Islands of Casco Bay on a Fully Private Charter

Casco Bay is home to more than 200 islands, each with its own character, history, and beauty. From the rocky shores of Eagle Island to the sandy beaches and quiet coves tucked between the outer islands, there’s always something new to discover. The best way to see it all is from the water on a fully private charter, at your own pace, with a captain who knows every corner of the bay.

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Islands and Destinations You Might Explore

Every island tour is built around your group and what you want to see. Our captains know Casco Bay inside and out and will put together a route that matches your interests, whether you want to cruise past working lobster boats, spot wildlife on remote ledges, or simply drift through quiet coves with a drink in hand.

Peaks Island

The most populated island in Casco Bay and a beloved Portland landmark. Peaks Island has a rich history, a tight-knit year-round community, and some of the best views of the Portland skyline you’ll find anywhere on the bay.

Eagle Island

Once the summer home of Arctic explorer Admiral Robert Peary, Eagle Island is now a Maine state historic site. The island sits in the outer bay and offers a fascinating glimpse into Maine’s history and natural beauty.

Cliff Island

The most remote of the year-round inhabited islands in Casco Bay, Cliff Island feels worlds away from the mainland. Quiet, rugged, and scenic, it’s a favorite for guests who want to explore the outer reaches of the bay.

Little Diamond and Great Diamond Islands

A pair of peaceful islands in the inner bay, both with stunning waterfront homes and a quiet, unhurried feel. Great Diamond Island is home to Diamond Cove, a former Army fort turned private community with some of the most beautiful grounds in Casco Bay.

House Island

A small, historic island in Portland Harbor home to Fort Scammel, one of the Civil War era fortifications built to defend the harbor. Rarely visited and virtually impossible to see without getting out on the water.

Hidden Coves and Remote Ledges

Some of the best spots in Casco Bay don’t have names on a map. Our captains know where to find the quiet anchorages, rocky ledges covered in seals, and tucked-away coves that most visitors never get to see.

Wildlife You Might See Along the Way

Casco Bay is home to an abundance of marine wildlife and your captain will keep an eye out throughout your charter. Common sightings include:

  • Harbor seals lounging on rocky ledges
  • Bald eagles perched high in the pines along the shoreline
  • Osprey diving for fish in the shallows
  • Harbor porpoises surfacing near the boat
  • Loons, cormorants, and a wide variety of seabirds
  • Lobster boats hauling traps along their routes
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Choose Your Island Tour

Not sure which is right for you? Contact us and we’ll help you choose based on what you want to see and do.

2-Hour Private Charter
$ 600
Perfect for groups who want to explore the inner islands and get a feel for Casco Bay. Your captain will cruise past Peaks Island, the Diamond Islands, and other highlights of the inner bay. Up to 6 guests.
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4-Hour Private Charter
$ 1,100
The complete Casco Bay island experience. With more time on the water your captain can venture into the outer bay to explore Eagle Island, Cliff Island, remote ledges, and hidden coves you won’t see on a shorter tour. Perfect for explorers and nature lovers. Up to 6 guests.
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Perfect For

Island tours are a great fit for a wide range of groups and interests.

  • Families with kids who love exploring and spotting wildlife
  • Nature lovers and birdwatchers
  • History enthusiasts interested in Maine’s island communities
  • Photography enthusiasts looking for dramatic coastal scenery
  • Visitors who want to experience the real Maine beyond the Old Port
  • Anyone who wants to get off the beaten path and see something truly special

What to Bring

Layers are always a good idea on the water even in summer, as the breeze can be cool once you get out into the bay. Bring sunscreen, sunglasses, and a camera. We provide light snacks, bottled water, and soft drinks on every charter. You’re welcome to bring your own food and drinks as well.